EP0368008A1 - Phénols contenant du fluor - Google Patents

Phénols contenant du fluor Download PDF

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Publication number
EP0368008A1
EP0368008A1 EP89118838A EP89118838A EP0368008A1 EP 0368008 A1 EP0368008 A1 EP 0368008A1 EP 89118838 A EP89118838 A EP 89118838A EP 89118838 A EP89118838 A EP 89118838A EP 0368008 A1 EP0368008 A1 EP 0368008A1
Authority
EP
European Patent Office
Prior art keywords
hydrogen
chlorine
radicals
formula
ocf3
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP89118838A
Other languages
German (de)
English (en)
Inventor
Ernst Dr. Kysela
Bernd Dr. Baasner
Klaus Dr. Schaller
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer AG
Original Assignee
Bayer AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Bayer AG filed Critical Bayer AG
Publication of EP0368008A1 publication Critical patent/EP0368008A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/84—Ketones containing a keto group bound to a six-membered aromatic ring containing ether groups, groups, groups, or groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/27—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups
    • C07C205/35—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C205/36—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system
    • C07C205/37—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system the oxygen atom of at least one of the etherified hydroxy groups being further bound to an acyclic carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/27—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups
    • C07C205/35—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C205/36—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system
    • C07C205/38—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system the oxygen atom of at least one of the etherified hydroxy groups being further bound to a carbon atom of a six-membered aromatic ring, e.g. nitrodiphenyl ethers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/42—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/44—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
    • C07C235/58—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring with carbon atoms of carboxamide groups and singly-bound oxygen atoms, bound in ortho-position to carbon atoms of the same non-condensed six-membered aromatic ring
    • C07C235/60—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring with carbon atoms of carboxamide groups and singly-bound oxygen atoms, bound in ortho-position to carbon atoms of the same non-condensed six-membered aromatic ring having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/10—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C323/18—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
    • C07C323/20—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton with singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
    • C07C43/23—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing hydroxy or O-metal groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C65/21—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups

Definitions

  • the present invention relates to new fluorine-containing phenols of the formula (I) in the one of the radicals R1 and R2 for OCF3, OCF2CFClH, OCF2CF2H, SCF2CF2H or SCF2CFClH and the other of the radicals R1 and R2 is hydrogen or C1 to C4 alkyl, R3 for hydrogen, chlorine or OCF3, R4 for hydrogen, C1 to C4 alkyl, NO2, chlorine, CONH2 or COOH and R5 represents hydrogen, chlorine or NO2, where one of the radicals R1 and R2 can also be SCF3 if R4 is NO2, CONH2 or COOH.
  • Preferred compounds of the formula (I) are those in which R1 for hydrogen, R2 for OCF3 or OCF2CFClH, R3 for hydrogen or chlorine, R4 for methyl, NO2, chlorine or CONH2 and R5 represent hydrogen, chlorine or NO2.
  • R1 for hydrogen, R2 for OCF3 or OCF2CFClH, R3 for hydrogen or chlorine, R4 for methyl, NO2 or chlorine and R5 represent hydrogen or chlorine.
  • a very particularly preferred compound of formula (I) is 2-methyl-4-trifluoromethoxy-benzene.
  • the fluorine-containing phenols according to the invention can be prepared in various ways.
  • a first method can be used in such a way that a phenol of the formula (II) in the R 2 'represents OCF3, OCF2CFClH, OCF2CF2H, SCF2CFClH or SCF2CF2H in the 2-position and optionally additionally in the 3- and / or 6-position substituents.
  • R 2 ' When introducing a NO2, COOH or CONH2 group in the starting phenol of formula (II) R 2 'can also stand for SCF3.
  • chlorine atoms can be introduced by reaction with a chlorinating agent.
  • a suitable chlorinating agent is e.g. elemental chlorine. Suitable temperatures for this are, for example, 0 to 50 ° C. It is convenient to work in the presence of a catalyst, e.g. Iron, and an inert solvent, e.g. a chlorinated hydrocarbon.
  • Nitro groups can be introduced, for example, by reaction with nitric acid. Depending on the reaction temperature and concentration of nitric acid, e.g. Introduce one (in 2-position) or two nitro groups (in 2- and 6-position).
  • a NO2 group can be introduced for example with 20 to 33 wt .-% nitric acid at 10 to 30 ° C, two NO2 groups for example with 37 to 60 wt .-% HNO3 at 50 to 80 ° C.
  • Carboxyl groups can be introduced, for example, by reaction with carbon dioxide under elevated pressure, at elevated temperature and in the presence of a base.
  • a suitable base is, for example, potassium carbonate, suitable pressures, for example those from 10 to 100 bar, suitable temperatures, for example those from 150 to 250 ° C.
  • Acid amide groups can be introduced, for example, by reacting any carboxyl groups introduced as described above, for example first in the presence of a solvent with SOCl2 and then with ammonia.
  • a second method in which an aniline of the formula (III) in which the radicals R1 to R5 have the meaning given for formula (I), diazotized and overcooked.
  • the diazotization can be carried out, for example, with sodium nitrite in the presence of hydrochloric acid, and the boiling, for example with azeotropic removal of water in the presence of sulfuric acid, at temperatures around 100 to 130 ° C.
  • This method is particularly suitable for the preparation of fluorine-containing phenols of the formula (I) in which R2 is OCF2CF2H or SCF2CF2H.
  • the reaction with tetrafluoroethylene is preferably carried out in the presence of a base and a dipolar, aprotic solvent, for example at temperatures in the range from 50 to 150.degree.
  • the new fluorine-containing phenols of the formula (I) according to the invention are important intermediates. They can be used, for example, with halogenated acetophenones of the type convert to acetophenones of the type halogenate them on the methyl group and by reacting the halogenation products with thiourea derivatives of the type substituted 2-aminothiazoles of the type obtained, which have a good activity against pests, in particular against fungi which damage plants.
  • 356 g (1.36 mol) of 3,4-bistrifluoromethoxy-aniline were added to 625 g of water and 332 g of concentrated hydrochloric acid diazotized with 246 g of 40% sodium nitrite solution.
  • the diazonium salt solution was added dropwise to a mixture of 520 g of water, 968 g of concentrated sulfuric acid and 1200 g of xylene in a temperature of 120 ° C. such that an internal temperature of 120 ° C. could be maintained there by azeotropically distilling off the water.
  • the xylene phase was then separated off and the 3,4-bistrifluoromethoxyphenol formed was isolated by extraction with an alkali solution. Distillation gave 200 g of product with a boiling point of 86 to 88 ° C at 25 mbar, which corresponds to 53% of theory.
EP89118838A 1988-10-24 1989-10-11 Phénols contenant du fluor Withdrawn EP0368008A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19883836175 DE3836175A1 (de) 1988-10-24 1988-10-24 Fluor enthaltende phenole
DE3836175 1988-10-24

Publications (1)

Publication Number Publication Date
EP0368008A1 true EP0368008A1 (fr) 1990-05-16

Family

ID=6365793

Family Applications (1)

Application Number Title Priority Date Filing Date
EP89118838A Withdrawn EP0368008A1 (fr) 1988-10-24 1989-10-11 Phénols contenant du fluor

Country Status (2)

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EP (1) EP0368008A1 (fr)
DE (1) DE3836175A1 (fr)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002048089A1 (fr) * 2000-12-12 2002-06-20 Ube Industries, Ltd. Procede de production de compose d'ether aromatique au mononitrate
WO2010057691A2 (fr) * 2008-08-11 2010-05-27 Solvay Solexis S.P.A. Hydrofluoroalcools ayant une stabilité thermique et chimique améliorée
US8722695B2 (en) 2009-12-11 2014-05-13 Autifony Therapeutics Limited Imidazolidinedione derivatives
US9133175B2 (en) 2010-12-06 2015-09-15 Autifony Therapeutics Limited Compounds
US9193704B2 (en) 2011-06-07 2015-11-24 Autifony Therapeutics Limited Hydantoin derivatives as KV3 inhibitors
US9422252B2 (en) 2012-05-22 2016-08-23 Autifony Therapeutics Limited Triazoles as Kv3 inhibitors
US9669030B2 (en) 2012-05-22 2017-06-06 Autifony Therapeutics Limited Hydantoin derivatives as Kv3 inhibitors
KR20220117977A (ko) * 2021-02-18 2022-08-25 중앙대학교 산학협력단 트리플루오로메틸화된 하이드로퀴논 유도체를 포함하는 항균제

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5104559A (en) * 1990-11-26 1992-04-14 The Dow Chemical Company Hydrogen perfluoroalkylaromatic ethers and related compositions and methods

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2312906A1 (de) * 1973-03-15 1974-09-19 Hoechst Ag Insektizide carbamate
EP0054149A1 (fr) * 1980-12-16 1982-06-23 BASF Aktiengesellschaft Esters d'acides trifluorométhoxy phényl (di) thiophosphoriques, leur procédé de préparation et leur utilisation comme pesticides
EP0091598A2 (fr) * 1982-04-08 1983-10-19 BASF Aktiengesellschaft Esters d'acides fluoroéthoxyphényl (di)thiophosphoriques, leur procédé de préparation et leur utilisation comme pesticides
EP0175188A1 (fr) * 1984-09-11 1986-03-26 Nihon Tokushu Noyaku Seizo K.K. Dérivés du carbamoylimidazole
DE3709609A1 (de) * 1987-03-24 1988-10-06 Hoechst Ag Verfahren zur herstellung von phenolen mit fluorhaltigen substituenten

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2312906A1 (de) * 1973-03-15 1974-09-19 Hoechst Ag Insektizide carbamate
EP0054149A1 (fr) * 1980-12-16 1982-06-23 BASF Aktiengesellschaft Esters d'acides trifluorométhoxy phényl (di) thiophosphoriques, leur procédé de préparation et leur utilisation comme pesticides
EP0091598A2 (fr) * 1982-04-08 1983-10-19 BASF Aktiengesellschaft Esters d'acides fluoroéthoxyphényl (di)thiophosphoriques, leur procédé de préparation et leur utilisation comme pesticides
EP0175188A1 (fr) * 1984-09-11 1986-03-26 Nihon Tokushu Noyaku Seizo K.K. Dérivés du carbamoylimidazole
DE3709609A1 (de) * 1987-03-24 1988-10-06 Hoechst Ag Verfahren zur herstellung von phenolen mit fluorhaltigen substituenten

Cited By (27)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002048089A1 (fr) * 2000-12-12 2002-06-20 Ube Industries, Ltd. Procede de production de compose d'ether aromatique au mononitrate
WO2010057691A2 (fr) * 2008-08-11 2010-05-27 Solvay Solexis S.P.A. Hydrofluoroalcools ayant une stabilité thermique et chimique améliorée
WO2010057691A3 (fr) * 2008-08-11 2010-10-14 Solvay Solexis S.P.A. Hydrofluoroalcools ayant une stabilité thermique et chimique améliorée
US8946136B2 (en) 2008-08-11 2015-02-03 Solvay Specialty Polymers Italy S.P.A. Hydrofluoroalcohols with improved thermal and chemical stability
US9849131B2 (en) 2009-12-11 2017-12-26 Autifony Therapeutics Limited Imidazolidinedione derivatives
US8722695B2 (en) 2009-12-11 2014-05-13 Autifony Therapeutics Limited Imidazolidinedione derivatives
US10632118B2 (en) 2009-12-11 2020-04-28 Autifony Therapeutics Limited Imidazolidinedione derivatives
US9216967B2 (en) 2009-12-11 2015-12-22 Autifony Therapeutics Limited Imidazolidinedione derivatives
US10058551B2 (en) 2009-12-11 2018-08-28 Autifony Therapeutics Limited Imidazolidinedione derivatives
US10555945B2 (en) 2010-12-06 2020-02-11 Autifony Therapeutics Limited Compounds
US9133175B2 (en) 2010-12-06 2015-09-15 Autifony Therapeutics Limited Compounds
US11583527B2 (en) 2010-12-06 2023-02-21 Autifony Therapeutics Limited Hydantoin derivatives useful as Kv3 inhibitors
US9833452B2 (en) 2010-12-06 2017-12-05 Autifony Therapeutics Limited Compounds
US11541052B2 (en) 2010-12-06 2023-01-03 Autifony Therapeutics Limited Compounds
US9346790B2 (en) 2010-12-06 2016-05-24 Autifony Therapeutics Limited Hydantoin derivatives useful as Kv3 inhibitors
US10098881B2 (en) 2010-12-06 2018-10-16 Autifony Therapeutics Limited Compounds
US10835534B2 (en) 2010-12-06 2020-11-17 Autifony Therapeutics Limited Compounds
US10265316B2 (en) 2010-12-06 2019-04-23 Autifony Therapeuctics Limited Hydantoin derivatives useful as Kv3 inhibitors
US9422272B2 (en) 2010-12-06 2016-08-23 Autifony Therapeutics Limited Compounds
US9193704B2 (en) 2011-06-07 2015-11-24 Autifony Therapeutics Limited Hydantoin derivatives as KV3 inhibitors
US10611735B2 (en) 2012-05-22 2020-04-07 Autifony Therapeutics Limited Triazoles as Kv3 inhibitors
US10160730B2 (en) 2012-05-22 2018-12-25 Autifony Therapeutics Limited Triazoles as KV3 inhibitors
US11180461B2 (en) 2012-05-22 2021-11-23 Autifony Therapeutics Limited Triazoles as Kv3 inhibitors
US9422252B2 (en) 2012-05-22 2016-08-23 Autifony Therapeutics Limited Triazoles as Kv3 inhibitors
US9669030B2 (en) 2012-05-22 2017-06-06 Autifony Therapeutics Limited Hydantoin derivatives as Kv3 inhibitors
KR20220117977A (ko) * 2021-02-18 2022-08-25 중앙대학교 산학협력단 트리플루오로메틸화된 하이드로퀴논 유도체를 포함하는 항균제
WO2022177078A1 (fr) * 2021-02-18 2022-08-25 중앙대학교 산학협력단 Agent antibactérien comprenant de l'hydroquinone trifluorométhylée

Also Published As

Publication number Publication date
DE3836175A1 (de) 1990-05-03

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